Acetoacetic Acid → HCID 178486676, compound

HRID 986640Notes

Reaction equation

HRID 986640 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([CH3:16])=[N:4][C:3]=1[OH:17].CC(CC(O)=O)=O.C(N(CC)CC)C.[C:32](Cl)(=[O:36])[CH:33]([CH3:35])[CH3:34]>C(Cl)Cl>[OH:17][C:3]1[N:4]=[C:5]([CH3:16])[C:6]2[C:11]([C:2]=1[NH:1][C:32](=[O:36])[CH:33]([CH3:35])[CH3:34])=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=2

Participants

6

Reactant 4

HCID 96Acetoacetic AcidHCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 178486674HCID 178486674, compound

Product 1

HCID 178486676HCID 178486676, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Amino-3-hydroxy-6,7-dimethoxy-1-methylisoquinoline (BBQ) (1.772 grams, 5 mmol) as the diacetate solvate in 50 ml methylene chloride was treated with 2.5 ml triethylamine (16.5 mmol) for 5 minutes and subsequently with 0.63 ml isobutyryl chloride (6 mmol) with stirring under a nitrogen atmosphere. After 1 hour, the slurry was evaporated to dryness in vacuo and boiled in 50 ml methanol and 5 ml water for 15 minutes. The solid was isolated by filtration, washed successively with methanol and acetone, and then dried in vacuo at 50° C. to provide 0.6 grams of Compound BO (39.4% yield) having a melting point of 292°-294° C. (with decomposition).

Workup

  1. customthe slurry was evaporated to dryness in vacuo
  2. wait5 ml water for 15 minutes
  3. customThe solid was isolated by filtration
  4. washwashed successively with methanol and acetone
  5. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-f6c0a230db7a4b09a9eac2d8cd7b61bb
Source dataset
uspto-grants-1987_12
Patent number
US04714705

Reaction notes

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